Sales Enablement Lead

Our mission is to increase the success rate of small businesses. Traditional banking has been a growth limiter rather than a growth enabler for business owners, and we’re changing that. Relay is the all-in-one, collaborative money management platform. We’re building for employer SMBs and their finance function, internal and external, and are focused on delivering a human-centric customer experience. Ultimately, we help SMBs be ‘on the money'.

We are looking for a Sales Enablement Lead to join our rapidly growing Sales team and drive operational excellence across the sales organization. You’ll play a pivotal role in defining and implementing the sales enablement strategy for BDR, AE, AM and sales leaders.

Joining Relay means a unique opportunity to make a huge impact by equipping our GTM team with the skills, systems, and insights to consistently drive high-quality sales conversations, accelerate time to value, and win with confidence in a buyer-led market. This is a high-impact, cross-functional role at the intersection of performance, process, and productivity. You’ll take full ownership of enablement, from onboarding and coaching to AI tools and playbook execution, empowering sellers to move quickly, learn faster, and close deals smarter. If you thrive on building scalable systems, simplifying complexity, and equipping others with the tools to win, then Relay is the place for you.

What You’ll Be Doing

• Own and scale onboarding, skill development, and role-readiness program while partnering with Sales, RevOps and Product Marketing to translate GTM priorities into repeatable behaviours
• Build scalable enablement systems using platforms, automation, and embedded intelligence
• Lead rep coaching through call shadowing, live deal support, and performance diagnostics, while building role-specific certifications, manager enablement programs, and internal mobility paths
• Translate sales friction into high-impact learning programs that drive conversion, speed, and confidence
• Operationalize sales playbooks, objection frameworks, and knowledge in tools like Notion, Gong, and Salesforce, while leveraging AI to personalize coaching and unlock real-time GTM insights
• Measure and report on enablement impact by tracking ramp time, attainment, forecasting accuracy, and rep productivity to drive continuous improvement
• Collaborate with Product Marketing on messaging, new product enablement, and vertical plays
• Work closely with RevOps on workflow optimization, CRM hygiene, and performance intelligence
• Align with CX and post-sale teams to drive adoption, expansion, and lifecycle selling
  
  

Who You Are

• You have 2+ years in a full-cycle, quota-carrying sales role (AE/BDR/AM) and 3+ years leading a sales or revenue enablement function, owning onboarding, coaching, and program design
• You have experience building enablement functions in a high-growth B2B SaaS environment (SMB-focused is a plus)
• You possess a strong understanding of modern selling techniques, such as buyer enablement, multithreading, negotiation, and value selling
• You are well-versed in the latest tech stack, with fluency in Salesforce, Gong, Notion, enablement metrics, and sales coaching platforms
• You bring expertise in executing impactful and engaging events, including SKOs, QBRs, and product launches
• You have experience designing and implementing career pathing programs (e.g. BDR to AE)
• You have the ability to simplify complex systems into clear, engaging enablement assets and experiences
• You are a strategic thinker with a builder mindset who thrives on turning ambiguity into systems that scale
  
  

Bonus Points

• You have experience in fintech, accounting software or a neobank
• You have worked with SMBs in North America
  
  

Our Commitment to You

• Competitive salary and meaningful equity: Relay employees are Relay owners, complete with equity and a competitive salary.
• Comprehensive health benefits: enjoy full health benefits from day one. We offer flexible Health or Wellness Spending Accounts and medical, dental, and vision coverage for you and your dependents.
• Flexible vacation and time off: every team member starts with 15 vacation days and 5 flex days to use as needed, plus an extra week of office closure during the end-of-year holidays so you can take time off to recharge and come back better for our customers.
• Parental leave with top-up: we offer 12 weeks off with a 100% salary top-up for all full-time employees, regardless of location, and accessible for all parents: birthing, non-birthing, and adoptive.
• Hybrid work environment: we value meaningful collaboration and connection at our Toronto office twice a week, with lunch, snacks, and beverages on us.
• Dog-friendly space: can dogs really make you happy and healthy? We don’t know for sure, but since we don’t want to chance it, our office is 100% floof-friendly.
• Personal and professional growth: through ongoing feedback, mentorship, and coaching, work with peers and leaders who are invested in your growth and success.
• Top-tier equipment: as a Mac-first company, our Toronto offices have everything you need to produce your best work comfortably, from multiple screens to ergonomic seating.
• Social connection: we believe in celebrating our wins with two annual company-wide get-togethers, quarterly team events, happy hours, and special events and networking opportunities with industry leaders.
  
  

The Interview Process

• Stage 1: A 30-minute Google Meet video call with a member of the Talent team
• Stage 2: A 45-minute Google Meet video call with the Director, Sales
• Stage 3: A 45-minute Google Meet video call with the Sales Leaders
• Stage 4: A 45-minute Google Meet video call with a member of the Leadership team
• Stage 5: A 30-minute live whiteboard exercise, followed by a 45-minute in-person discussion with our Sales team
  
  

Why Relay Might Be the Perfect Fit For You

• You push relentlessly for reinvention: You’re built to constantly ask, “How can this be better?” Change excites you and you drive it.
• You crave autonomy: We trust our team with big challenges and the freedom to solve them. If you’re someone who takes initiative, is comfortable taking risks, and seeks input when needed, you’ll find the freedom here empowering.
• You own your work: You take pride in your work, follow through on commitments, and feel a deep sense of responsibility for outcomes, not just tasks.
• You treat comfort as a red flag: You seek growth. When things feel too comfortable, you lean into change. You’re excited about stepping into the unknown and navigating new terrain to create something better alongside your team.
• You care about impact, not noise: You care deeply about the substance of your work. You measure success by results, not recognition and you let your work speak for itself.
• You’re energized by complexity and ambiguity: You enjoy tackling problems that don’t come with a playbook. You’re comfortable building from scratch, iterating as you go, and collaborating to shape the best path forward.
• You seek out feedback: We value directness, clarity, and respect. We believe honesty fuels great work and career growth. You see feedback as a tool for learning and improvement, and you know that open, honest dialogue is key to achieving the best results — together.
• You’re here for more than a job: At Relay, everything we do is in service of our mission to help small businesses thrive. To drive impact and have purpose here, that mission must matter to you too.
  
  

Our Promise

We’re driving real change for small business owners, powered by truly remarkable people. At Relay, you’ll find the confidence to take chances, trust to take initiative, and the support you need to build a career you love. Here, we make sure every team member feels empowered to make big decisions, encourage to ask tough questions, and challenged to take risks that result in work we’re all proud of. We give you the baton–you run the Relay.

What’s Important To Us

Research shows that women-identifying and other marginalized individuals often apply only if they meet 100% of the qualifications. But no one is a perfect match on paper. If this role excites you, we’d love to hear from you and figure out together if it’s a great fit.

At Relay, we believe that diversity is key to building high-performing teams, and creating an inclusive work environment is our priority. We are an equal opportunity employer and welcome people of diverse backgrounds, perspectives, and skills.

We will work with applicants to provide accommodations at any stage of the hiring process. If you require accommodations during the interview process, please email your Talent Partner, and we will work with you to meet your needs.